Potassium Hydroxide → (S)-1-[[(R)-alpha-methyl-p-[2-(4-phenyl-1-piperazinyl)ethoxy]phenethyl]amino]-3-phenoxy-2-propanol

HRID 973764Notes

Reaction equation

HRID 973764 reaction equation
[OH:1][CH:2]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][NH:4][C@H:5]([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[OH-].[K+].Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>C(O)CC>[CH3:14][C@@H:5]([NH:4][CH2:3][C@H:2]([OH:1])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 47418781-(2-Chloroethyl)-4-phenylpiperazineHCID 67905865p-[(R)-2-[[(RS)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenol

Product 1

HCID 18647796(S)-1-[[(R)-alpha-methyl-p-[2-(4-phenyl-1-piperazinyl)ethoxy]phenethyl]amino]-3-phenoxy-2-propanol

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 0.5 g of p-[(R)-2-[[(RS)-2-hydroxy-3-phenoxypropyl]amino]propyl]phenol, 185 mg of potassium hydroxide, 410 mg of 1-(2-chloroethyl)-4-phenyl-piperazine and 15 ml of n-propanol was heated to 60° for 2.5 hours. The reaction mixture was poured on to ice-water and extracted with ethyl acetate. After evaporation of the solvent and chromatography of the crude product on silica gel with chloroform/n-propanol/saturated ammonia (1000:10:1) there were obtained 340 mg of pure, amorphous (S)-1-[[(R)-α-methyl-p-[2-(4-phenyl-1-piperazinyl)ethoxy]phenethyl]amino]-3-phenoxy-2-propanol, [α]D20 =-19° (c=0.8 in methanol), ε222 =21890.

Workup

  1. temperaturewas heated to 60° for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. customAfter evaporation of the solvent and chromatography of the crude product on silica gel with chloroform/n-propanol/saturated ammonia (1000:10:1) there

Sources & evidence

ORD record
ord-9307c7ca2e52426590bdb35f3b7dcea0
Source dataset
uspto-grants-1991_11
Patent number
US05064863

Reaction notes

Loading…